


Do I Deserve

by CostumersDelight (CostumerDelight)



Category: Critical Role (Web Series)
Genre: Caleb Widogast Deserves Nice Things, Caleb is a sub, Canon Compliant, Essek is a dom, Light Dom/sub, M/M, Plot What Plot, Porn Without Plot, Porn with Feelings, Praise Kink, Sort Of, What if Beauregard didn't cock block Caleb Widogast?, implied previous relationships, implied punishment kink, spoilers for ep 91
Language: English
Status: Completed
Published: 2020-01-18
Updated: 2020-01-18
Packaged: 2021-02-27 12:42:10
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 3,549
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22307359
Author URL: https://archiveofourown.org/users/CostumerDelight/pseuds/CostumersDelight
Summary: "It is just us, you do not need to float," Caleb points out then, and Essek stops just outside of Caleb's vision, only the hem of the mantle giving away his location. "I already know your predicament and position, and after what you have divulged to us this evening, you do not need to keep up appearances around us.""That is a fair point," he says from somewhere behind Caleb, the sound slightly off in direction from what he can tell, "but you should know by now that this is different than either of those.”A hand traces up Caleb's neck and he tenses however much he can, the cool touch sending shocks to his core; he hadn’t noticed as his scarf was removed from his shoulders, so focused on keeping his voice relaxed. Essek's mantle is still unnervingly just at the edge of Caleb's sight, and he desperately wants to turn to look at Essek, but it isn't part of the script.Because of course there was a script to this song and dance they created.
Relationships: Essek Thelyss/Caleb Widogast
Comments: 14
Kudos: 333





	Do I Deserve

**Author's Note:**

> I was so upset by Beauregard's COCK BLOCKING this recent episode, I had to make it right for the Shadowgast fans.

"Beauregard," Caleb asks cautiously, "did you really need to come with? I am capable of getting back home on my own." They walk a few paces behind Essek, who is gliding ahead of them leading the way to his home from the Xhorhaus

"Oh, yeah, no, sure," Beau chuckles, shrugging next to him. "I just wanted to see his place real quick. You know. In case you're locked up studying again and we need to get Essek."

"But Jester's sending spells…" Caleb tries to argue, but she gives him a gentle shove.

"If she's tapped or didn't have it ready or something. Backup plans, man." Beauregard smirks, catching up with Essek and talking quietly with him.

Caleb sighs into his hand as it pulls it down his face, noting that his beard stubble was getting long again. With Yasha back, maybe he could ask her to help him trim it again? That thought gets pushed aside when he catches Essek's eye, staring back at him while Beau is saying something about fathers.

Bren Aldric Ermandrud has been in love before, but Caleb Widogast has not yet had the pleasure. With all his focus being put towards survival and hiding, and protecting Nott upon their meeting and subsequent adventures, he hadn't had time to consider romance, or even so much as a passing one night stand. At least, not until the gnoll mines, and the pinprick of happiness he received from the press of lips on his forehead amidst the chaos of flames. Even if it had followed a sharp slap to his face.

But now, Caleb has shed his guise that hides him from his fears, for they have already been made aware of his actions, and he has not just one, but two government bodies holding him in high regard, and the demon of his past can't do a single thing about it. And Caleb has found himself not just entranced by the magicks within the country, but also by the people, and particularly the drow ahead of him, who still has an eye peering back over his mantle at him.

They come to the gated yard of the three towers that comprised Essek's home, and Caleb stares up at the spires of it, mesmerized by the intricate rings, the details of it and the beauty.

"Thank you for the escort, but now I shall take my leave," Essek is saying, snapping Caleb out of his thoughts. "Have a pleasant evening."

"Shadowhand Essek," Caleb starts, but the billowing mantle swings slightly, a hand rising to give him pause.

"Just Essek, we have shared in food and wine," the Shadowhand smiles, "the least we can do now is address one another by given name. And I have no title to call you all by, so just Essek will do."

"...Essek, then," Caleb says, the familiarity without a title giving him a slight thrill, "there was something I wished to speak with you about in private, if that is alright." Essek just nods, looking expectantly at Beauregard. "Beau, I will meet you back at the Xhorhaus,  _ ja _ ?"

"I can wait here," she says plainly, leaning now on the fence. "You two go talk your nerd stuff or whatever." She yawns and turns to face the road.

"Very well, then, please follow me," Essek smiles, gesturing for Caleb to follow behind him. The door swings open without being touched, allowing them entry, and it swings back behind Caleb, closing with a soft thud. "You wished for privacy, and here we are. What can I help you with, Caleb?"

"I… what really made you wish to come to dinner tonight?" Caleb says, keeping his face stoic. "Caduceus is a wonderful cook, but you would seem to have a more refined palate based on your wine choice as a gift."

"You are indeed quite perceptive, Caleb." Essek is still floating as he takes a wide berth around Caleb, as if inspecting him, but his eyes are focused elsewhere, on the wall behind him and not quite meeting Caleb's gaze. "Yes, the wine was a gift for your house as is generally proper for social visits in Xhorhas between dens. And perhaps I was relieved to see that you and your friends had returned safely from Rexxentrom and the Empire as a whole.” He makes a quick hand gesture as he speaks, and Caleb knows the spell; but he lets it happen. He’s held in place, just his head able to move. A spell that Essek had once told him he used during interrogations.

"It is just us, you do not need to float," Caleb points out then, and Essek stops just outside of Caleb's vision, only the hem of the mantle giving away his location. "I already know your predicament and position, and after what you have divulged to us this evening, you do not need to keep up appearances around us."

"That is a fair point," he says from somewhere behind Caleb, the sound slightly off in direction from what he can tell, "but you should know by now that this is different than either of those.”

A hand traces up Caleb's neck and he tenses however much he can, the cool touch sending shocks to his core; he hadn’t noticed as his scarf was removed from his shoulders, so focused on keeping his voice relaxed. Essek's mantle is still unnervingly just at the edge of Caleb's sight, and he desperately wants to turn to look at Essek, but it isn't part of the script.

Because of course there was a script to this song and dance they created.

"Yes, Sir," Caleb murmurs, feeling the hand gently scrape at his neck as a reward, eliciting shivers that run all the way down his back.

"Very good, you remembered," Essek praises, just beside his ear. “That was a very clever ruse for Beauregard, but we won’t be able to do very much if she is waiting outside. So when I let you go, you will message her and tell her your question is a bit more involved and you may be quite some time.”

“And if she says she will still wait?” Caleb replies; he knows how Beauregard thinks, to a degree, and she would certainly stay put if she had any doubts about Essek’s intentions.

“You’re a charming man, Caleb, I’m sure you can figure out how to get her to understand.” Essek snapped his fingers, the spell dropping and Caleb taking a half-step forward. “When you are finished, my chambers are upstairs on the right.” And Essek glides up the staircase, leaving Caleb in the entryway. He fumbles out the little copper wire and adjusts his angle to where Beauregard should have been.

“Ah, Beauregard, my inquiry is perhaps a bit more complex than I expected, and Essek is fetching some books to help answer it, so I will be much longer than I thought,” he says, watching the wire sparkle as it relays its message. Hoping it would be enough, he starts up the stairs before Beauregard responds.

“ _ I know Undercommon, should I come in and help him look through his books? _ ”

“ _ Nein _ , Beauregard, we have it handled, but I do not wish for you to be waiting so long outside of Essek’s home, there could be Empire spies watching,” he pulls out the wire to message again, pausing on the floating glass sheets.

“ _ Caleb, stop lying, I know exactly what he wants with you, and what you want with him. _ ” Caleb can hear the smirk in her voice.

“Beauregard, please, I will meet you back at the house with the others, you don’t need to wait for me here,” Caleb pleads then, “and please do not tell the others?”

“ _ You owe  _ me _ a favor for that, then _ ,” she replies.

Caleb can’t know for sure if she leaves, but he hurries up the stairs towards the room that Essek had directed him to go. No one is within the chambers, so Caleb takes in the grand, yet simplistic room. He knows that Essek is a drow, an elf, and that elves generally did not require sleep like other humanoids, having developed the ability to meditate and trance for their rest; so the large bed in the room is a surprise to him, tall posts on each corner that curve to meet in the middle above the bed, all but the foot and one side of it obscured with a deep navy, gossamer curtain. The bedding is stark silver-gray in contrast. There is a wardrobe to the side made of the same purple-toned wood that much of Rosohna was built with, and a full length mirror framed in silvers and purple wood next to him where he entered the room, along with a dressing table also in those purple hues.

“Surprised?” Essek’s voice is on his shoulder again, and Caleb jolts a bit; he hadn’t noticed the door on the other side of the bed, hidden from view by the canopy, and Essek has glided up behind him again from the now-open doorway. “I don’t usually bring many people to this room, to be fair, so I’ve never felt the need to decorate it in any meaningful fashion. As I’ve said this evening already, I tend to cherish my solitude.”

“I see, that is…” Caleb starts, but there’s a directing hand on the small of his back, leading him towards the bed.

Caleb had entertained the idea of becoming intimate with another person following the mines, but a part of that had been ripped away when they had the unfortunate incident on Glory Run Road where they lost one of their friends; he considers proposing a visit once in a while, but he is himself uncertain whether or not it is a good idea, and files it away for another time. It was out at sea that he vaguely considered another of his companions, making a promise and a blood pact, but that fell to the wayside after a few days.

It wasn’t until they had arrived in Rosohna and went to the Brightqueen’s court that someone had taken his fancy again. Being introduced to Shadowhand Essek Thelyss and being put in his care and supervision had been an interesting exchange, following the original presentation; himself and Beauregard, the only humans in their party, being wrapped up like they were possessions. He had caught the eye of the Shadowhand while in those straps, and there was a recognizable hunger in his eyes until Fjord cut the leather away and Caleb instictively rubbed at his wrists, averting his gaze from the drow until he was called up to guide them.

“Are you comfortable?” Essek asks, breaking Caleb’s train of thought again. He has been divested of his clothes and lays on the pale sheets, Essek standing over him with only his shirt removed. Caleb gives a few tugs to the restraints on his arms and legs, testing them, before nodding to Essek. “Good. And if you wish to stop?”

“Conjuration.”

“Very good,” Essek hums in approval, ghosting a hand up Caleb’s bare thigh to his hip. “You’re still willing in this?”

“Yes, very much so,” Caleb assures him breathlessly, and is treated with a soft smile that makes his heart flip for a moment, before it goes to a cool, stoic expression, with just a hint of mischief behind the faint lilac of the drow’s eyes.

“I’m so pleased to hear that,” he says then, his voice sultry and enticing; but Caleb doesn’t even hear it as the hand on his hip ghosts up the vein on the underside of his dick, already hard from anticipation of the evening’s events. He shudders out a breath when the hand is removed from him, and he watches Essek as he settles onto the bed, drifting a hand through the air and pulling something from it. “I’m honestly quite surprised you were amenable to this arrangement, Caleb,” he starts, almost talking to himself rather than to Caleb as he opens the small pot of lubricant and replaces it in his pocket dimension, “especially so early on in our acquaintance. It made me wonder a bit about you.”

“How so? That I would not enjoy the company of a handsome drow?” Caleb huffs out, earning himself a little slap to the inside of his thigh. “Sir?” he adds on after, trying to suppress his grin.

“Flattery will get you everywhere, Caleb, but only if you know how to use it,” Essek chides him. “In any case, yes, in part. But I have also seen the pain in your eyes.” Caleb tenses at that, and Essek continues, “You seem to be seeking out something to ease that pain. And in turn, I hope I’ve been able to help ease some of that.” Essek drops a hand to Caleb’s cock, then, coating it in the lubricant and stroking it. Caleb relaxes into the touch and moans softly.

When he had finally,  _ finally _ gotten Essek to agree to teach him a dunamantic spell, Caleb was elated. He had filled his desk in the Xhorhaus with new supplies and spent quite some time reorganizing it before posing the question. He had removed his coat when they had gone into the library and rolled his sleeves up, his excitement making him forget the scars on his arms until Essek had stalled in his explanations and commented about them.

_ “So this was an accident as a child?” Essek had clarified, and Caleb nodded, affirming his lie. “It seems quite regular for an accident, Mister Caleb.” _

_ “Ah, you can just call me Caleb,” he said at that moment, a small pang of guilt and regret coming from the title. “And yes, it was, ah…” _

_ “Alright then, Caleb,” Essek nodded back, tapping his fingers rhythmically on the desk, “I won’t pressure you for the truth, but let me make one thing clear. I do not appreciate being lied to.” Essek clenched his hand on Caleb’s, a threat in his voice. “I will not teach you anything if you deem it necessary to lie to me. I can and will accept if you say you aren’t comfortable sharing something with me. I will not begrudge you for that. But for me to trust you with this magic, you must trust me in return.” _

_ “Yes, sir,” Caleb said softly. Essek tensed his hand, relaxing it after a moment and patting Caleb’s hand. “I apologize. It’s a very tender subject to me. I only just was able to go without wrappings on my hands to hide them.” _

_ “You don’t have to explain right now,” Essek replied, his voice lower and softer, almost nurturing in a way. “But keep it in mind for the future. I do have one more question before we get back to work on this, though…” _

That question had prompted their regular study sessions, and their regular sexual encounters. Caleb had admitted that he wanted to be dominated during their first tryst, and Essek had obliged, even to some of Caleb’s darker requests as time went on. But with how gentle Essek is being with him now, Caleb knows their usual routine is off the table.

“E-Essek,” he breaths out, whimpering with the slow pace of the drow’s hand stroking and pumping his dick. “Pl-please, sir…”

“Shh, I’ve got you, Caleb,” Essek hushes him, his other hand tracing sigils up on Caleb’s shoulder; nothing being cast, but a soothing touch and driving Caleb’s nerves on fire. “Tonight I saw your pain when I brought up my parents. It made some of my research fall into place when I was gathering information, and a lot of things make sense now.”

He twists his hand slightly, wringing out another moan from Caleb. Precome is glistening on his tip, and Essek shifts again over him, settling between Caleb’s legs. With a bit of effort, he manages to lift Caleb’s knees over his shoulders and takes Caleb’s dick in hand again, stroking the entire length as he stares down at Caleb.

“Will you let me take care of you, tonight?” Essek asks softly, and Caleb, already nearing his limit, almost comes from the tenderness of the sentiment as he nods. Essek has no further reservations as he takes Caleb’s cock in mouth and gently sucks, hollowing his cheeks. Caleb’s broken moan is silenced by Essek’s free hand dipping into his mouth. Caleb laves them with his tongue, desperately keeping his hips from bucking up into the heat of Essek’s mouth.

Essek’s lubricated hand moves to Caleb’s flank, gently sliding a finger across his hole and pressing at him. Caleb whines around the fingers in his mouth, mirroring to the best of his ability how Essek swirls his own tongue about Caleb’s cock. The next press of his fingers to Caleb’s entrance, he bucks slightly and one digit slides in, Caleb gasping at the intrusion. Essek took the moment to pull his fingers from Caleb’s mouth and undo his own pants, slipping out of them easily and slicking himself up.

“I’m… I’m so close…” Caleb whines as Essek pops off his cock with an obscene sound.

“I know, I know,” Essek says soothingly, placing a kiss to the inside of Caleb’s knee. “I’ve got you, don’t worry. You’re doing so well, Caleb.”

He cries out slightly, shuddering at the praise and whimpering, looking up at Essek as he gazes back, enraptured and adoring. He adds another slick finger to Caleb’s heat, replacing his other hand to Caleb’s cock and stroking it languidly, murmuring praises against the human’s leg and kissing it between words. It’s not until he adds a third finger and begins pressing against Caleb’s prostate that Caleb finds his voice again.

“Please… Please, Essek…” he begs, feeling himself flush to his ears. He knows he looks completely debauched, an utter mess; it’s not different from any other time he’s been at Essek’s mercy, but this slow act feels to him almost loving and worshipful, and Caleb’s broken soul is crying at the care he’s being shown in this moment. “Please…” Essek nods and lowers Caleb’s hips to his own lap, gently rubbing his thighs and stomach.

“I’m going to enter you now, alright?” Essek says gently, slicking his own cock again and pressing the tip to Caleb’s ass. “Let me know if it hurts at all.”

“ _ Essek _ ,” Caleb moans, thrusting his hips to meet Essek and take in the head of Essek’s cock, gasping against the soft pressure.

“You’re very impatient,” Essek chuckles, slowly thrusting in deeper until their bodies were flush together, Essek panting with Caleb’s leg’s spread open around him. “You’re wonderful, Caleb, you know that, right?” Caleb’s breath hitches, his eyes blowing wide in shock. “You’re hard on yourself, and you want others to be hard on you, to punish you, but you deserve to have nice things, Caleb Widogast.” Essek bends over Caleb, bringing his face close enough for his breath to ghost over Caleb’s cheek as he starts thrusting again, burying himself into Caleb and shooting pleasure up through Caleb’s entire body with a hand now pumping Caleb’s cock in time with his thrusts.

Caleb strains against the restraints on his arms, his desperate whimpers urging Essek to free his arms for the first time since they’ve started this unconventional arrangement. Essek obliges him, and soon Caleb has his arms wrapped around Essek’s shoulders, pulling him closer and gasping as one, two, three more thrusts has him blinded by white hot pleasure, spilling himself between their bodies and crying out; a cry silenced as Essek covers his mouth with a searing kiss, swallowing the wailing and moans.

Caleb feels the aches of his body as he returns to it, body chilled with cooling sweat. Essek has vanished, but when Caleb starts to shift to look for him, a warm cloth is touched to his stomach and he jumps at it, looking up the arm to see the soft gaze boring into him from the drow.

“Sorry, I didn’t mean to startle you,” Essek hummed softly, wiping up the mess that coated Caleb’s front. “I know I’ve just magicked you clean before, but…” He shrugs, giving Caleb a smile.

_ Do I really deserve your kindness? _ Caleb thinks, relaxing at the gentle swipes of the cloth.

“You do, I promise,” Essek replies, and Caleb feels a new flush cover his body, bringing his hands up to cover his face. “Caleb, let me see you,” Essek asks quietly, gently touching one of Caleb’s wrists. It takes him a few moments before Caleb lets his hands fall away from his face, but he stares off instead at the wardrobe. “You deserve nice things, and if my kindness is a nice thing, then you deserve it more than you know.”

“...are you a nice thing I deserve?” Caleb mumbles despite himself, then, his emotions already having bubbled up towards the surface while Essek fucked… no,  _ made love _ to him, with him. That question seems to give Essek pause, and Caleb takes that moment to look back to the drow, who is flushing an unfair shade of violet. “Would… would that be alright?”

“Of course, Caleb, if you would have me,” Essek smiles. Caleb brings his hand to cup Essek’s face and pulls him into a gentle kiss.


End file.
